Mezlocillin (CED0007094)

Record Information
Version1.0
Creation Date2016-05-22 03:43:44 UTC
Update Date2026-08-21 19:12:06 UTC
Accession NumberCHEM016789
Identification
Common NameMezlocillin
ClassSmall Molecule
Description
Mezlocillin is a compound with the chemical formula C21H25N5O8S2. Mezlocillin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 539.58 g/mol, Mezlocillin is a heavy molecule. The compound is found in or released from three recorded sources: food, food processing & cookware (processing meats), electrical & electronic equipment (video games), and healthcare, pharmaceuticals & veterinary products (antibiotics). Recorded routes of exposure include oral and inhalation. In terms of biological activity, Mezlocillin has four recorded protein targets. It acts as a binder or inhibitor of penicillin-binding protein 1A (pbpA), serine-type D-Ala-D-Ala carboxypeptidase (pbp3), peptidoglycan D,D-transpeptidase MrdA (mrdA), and peptidoglycan D,D-transpeptidase FtsI (ftsI).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulfonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6beta-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidChEBI
MezlinChEBI
MezlocilinaChEBI
MezlocillineChEBI
MezlocillinumChEBI
(2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulfonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
(2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulphonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
(2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulphonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidGenerator
6b-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator
6b-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator
6b-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator
6b-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator
6beta-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator
6beta-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator
6beta-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator
6Β-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator
6Β-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator
6Β-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanateGenerator
6Β-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acidGenerator
Bayf 1353HMDB
Curasan brand OF mezlocillin sodium (sterile)HMDB
BaypenHMDB
MelocinHMDB
Sodium, mezlocillinHMDB
Mezlocillin sodiumHMDB
Bay F 1353HMDB
Bay-F 1353HMDB
Bayer brand OF mezlocillin sodium (sterile)HMDB
MeslocillinHMDB
Chemical FormulaC21H25N5O8S2
Average Molecular Mass539.582 g/mol
Monoisotopic Mass539.114 g/mol
CAS Registry Number51481-65-3
IUPAC Name(2S,5R,6R)-6-[(2R)-2-[(3-methanesulfonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namemezlocillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(C1=O)S(C)(=O)=O)C1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12-,13-,14+,17-/m1/s1
InChI KeyYPBATNHYBCGSSN-VWPFQQQWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • N-carbamoyl-alpha-amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Penam
  • Sulfonylurea
  • Monocyclic benzene moiety
  • Imidazolidinone
  • Benzenoid
  • Beta-lactam
  • Imidazolidine
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • Urea
  • Azetidine
  • Secondary carboxylic acid amide
  • Carbonic acid derivative
  • Lactam
  • Carboxamide group
  • Hemithioaminal
  • Dialkylthioether
  • Thioether
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP0.21ALOGPS
logP-0.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area173.5 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.88 m³·mol⁻¹ChemAxon
Polarizability51.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-1090000000-30ba63db4797e4d4836dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-1090000000-8356c0b1a87fcce856cfNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0910010000-9de4bf02d7dd1cc9d377Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-7910000000-e06a9bd362ce4723bce2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-6900000000-f20f6eeb80ce786a597dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0109200000-4b61d69c53d74fe2e0a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-3908300000-41e54898cd272dbc82ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9311000000-fd81fa067ad63b9dc4d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0432090000-edbf59d4f68de248dc62Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-3925010000-5a77477e443c073ce3f2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-0913100000-38849f0b13c1ff924b58Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1902030000-431dbf04e41622d870c4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9500000000-6bd2926f658df74e070eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fu-7910000000-2183d83c42f1b7c12ac4Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6546.0Log mg/kg[3700:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
552Processing MeatsFood, food processing & cookwareNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Mezlocillin Drug Metabolism Action Pathway
Mezlocillin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.389246
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)347.986
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.233548
Baculoviral IAP repeat-containing protein 2 structureClick to view 3D structureBaculoviral IAP repeat-containing protein 2Q13490HumansPredicted (SEA)23.5105
Baculoviral IAP repeat-containing protein 8 structureClick to view 3D structureBaculoviral IAP repeat-containing protein 8Q96P09HumansPredicted (SEA)13.3122
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.544945
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.544945
E3 ubiquitin-protein ligase XIAP structureClick to view 3D structureE3 ubiquitin-protein ligase XIAPP98170HumansPredicted (SEA)75.903
Click to view 3D structureProcathepsin LP07154Rattus norvegicusPredicted (SEA)60.0218
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)357.484
Baculoviral IAP repeat-containing protein 3 structureClick to view 3D structureBaculoviral IAP repeat-containing protein 3Q13489HumansPredicted (SEA)47.7216
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)17.6718
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)5914.44
Cathepsin K structureClick to view 3D structureCathepsin KP43235HumansPredicted (SEA)942.287
Click to view 3D structurePlasmepsin IIIQ9Y006Plasmodium falciparumPredicted (SEA)25.8459
Click to view 3D structureProteaseQ82323Human T-lymphotropic virus 1Predicted (SEA)84.7
Click to view 3D structureProteaseQ82134Human T-cell leukemia virus type IPredicted (SEA)84.8557
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)516.841
Cathepsin D structureClick to view 3D structureCathepsin DP07339HumansPredicted (SEA)623.65
11-beta-hydroxysteroid dehydrogenase 1 structureClick to view 3D structure11-beta-hydroxysteroid dehydrogenase 1P28845HumansPredicted (SEA)272.706
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)6236.42
Cathepsin S structureClick to view 3D structureCathepsin SP25774HumansPredicted (SEA)1292.61
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)3568.3
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)97.0001
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)32.4631
Concentrations
Not Available
External Links
DrugBank IDDB00948
HMDB IDHMDB0015083
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMezlocillin
Chemspider ID570894
ChEBI ID6919
PubChem Compound ID656511
Kegg Compound IDC07221
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6460964
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9403281
5. McCormick PA, Greenslade L, Kibbler CC, Chin JK, Burroughs AK, McIntyre N: A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients. Hepatology. 1997 Apr;25(4):833-6.
6. Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B: Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure. Eur J Clin Pharmacol. 1997;53(2):111-5.
7. Kristof RA, Clusmann H, Koehler W, Fink KB, Schramm J: Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange. J Neurol Neurosurg Psychiatry. 1998 Mar;64(3):379-81.